2000s Rom Coms and Chick Flicks
by krmickey | created - 01 Jan 2020 | updated - 2 weeks ago | Public- Instant Watch Options
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1. It's Complicated (2009)
R | 120 min | Comedy, Drama, Romance
When attending their son's college graduation, a couple reignite the spark in their relationship. But the complicated fact is they're divorced and he's remarried.
Director: Nancy Meyers | Stars: Meryl Streep, Steve Martin, Alec Baldwin, John Krasinski
Votes: 98,517 | Gross: $112.74M
2. America's Sweethearts (2001)
PG-13 | 102 min | Comedy, Romance
A movie publicist deals with the messy public split of his movie's co-stars while keeping reporters at bay while a reclusive director holds the film's print hostage.
Director: Joe Roth | Stars: Julia Roberts, John Cusack, Billy Crystal, Catherine Zeta-Jones
Votes: 60,365 | Gross: $93.61M
3. Heartbreakers (2001)
PG-13 | 123 min | Comedy, Crime, Romance
A mother and daughter con team seduce and scam wealthy men.
Director: David Mirkin | Stars: Sigourney Weaver, Jennifer Love Hewitt, Gene Hackman, Ray Liotta
Votes: 58,008 | Gross: $40.34M
4. The Nanny Diaries (2007)
PG-13 | 105 min | Comedy, Drama, Romance
A college graduate goes to work as a nanny for a rich New York family. Ensconced in their home, she has to juggle their dysfunction, a new romance, and the spoiled brat in her charge.
Directors: Shari Springer Berman, Robert Pulcini | Stars: Scarlett Johansson, Laura Linney, Paul Giamatti, Donna Murphy
Votes: 64,091 | Gross: $25.93M
5. Mamma Mia! (2008)
PG-13 | 108 min | Comedy, Musical, Romance
The story of a bride-to-be trying to find her real father told using hit songs by the popular 1970s group ABBA.
Director: Phyllida Lloyd | Stars: Meryl Streep, Pierce Brosnan, Amanda Seyfried, Stellan Skarsgård
Votes: 274,453 | Gross: $144.13M
6. Love Actually (2003)
R | 135 min | Comedy, Drama, Romance
Follows the lives of eight very different couples in dealing with their love lives in various loosely interrelated tales all set during a frantic month before Christmas in London, England.
Director: Richard Curtis | Stars: Hugh Grant, Martine McCutcheon, Liam Neeson, Laura Linney
Votes: 531,604 | Gross: $59.70M
7. The Wedding Planner (2001)
PG-13 | 103 min | Comedy, Romance
Mary Fiore is San Francisco's most successful supplier of romance and glamor. She knows all the tricks. She knows all the rules. But then she breaks the most important rule of all: she falls in love with the groom.
Director: Adam Shankman | Stars: Jennifer Lopez, Matthew McConaughey, Bridgette Wilson-Sampras, Justin Chambers
Votes: 86,556 | Gross: $60.40M
8. Forgetting Sarah Marshall (2008)
R | 111 min | Comedy, Drama, Romance
Devastated Peter takes a Hawaiian vacation in order to deal with the recent break-up with his TV star girlfriend, Sarah. Little does he know, Sarah's traveling to the same resort as her ex - and she's bringing along her new boyfriend.
Director: Nicholas Stoller | Stars: Kristen Bell, Jason Segel, Paul Rudd, Mila Kunis
Votes: 302,512 | Gross: $63.17M
9. The Proposal (I) (2009)
PG-13 | 108 min | Comedy, Drama, Romance
A pushy boss forces her young assistant to marry her in order to keep her visa status in the U.S. and avoid deportation to Canada.
Director: Anne Fletcher | Stars: Sandra Bullock, Ryan Reynolds, Mary Steenburgen, Craig T. Nelson
Votes: 360,460 | Gross: $163.96M
10. Knocked Up (2007)
R | 129 min | Comedy, Romance
For fun-loving party animal Ben Stone, the last thing he ever expected was for his one-night stand to show up on his doorstep eight weeks later to tell him she's pregnant with his child.
Director: Judd Apatow | Stars: Seth Rogen, Katherine Heigl, Paul Rudd, Leslie Mann
Votes: 384,709 | Gross: $148.73M
11. Just My Luck (2006)
PG-13 | 103 min | Comedy, Fantasy, Romance
Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.
Director: Donald Petrie | Stars: Lindsay Lohan, Chris Pine, Samaire Armstrong, Bree Turner
Votes: 61,601 | Gross: $17.32M
12. Hitch (I) (2005)
PG-13 | 118 min | Comedy, Romance
A smooth-talking man falls for a hardened columnist while helping a shy accountant woo a beautiful heiress.
Director: Andy Tennant | Stars: Will Smith, Eva Mendes, Kevin James, Amber Valletta
Votes: 335,485 | Gross: $179.50M
13. 13 Going on 30 (2004)
PG-13 | 98 min | Comedy, Fantasy, Romance
Unpopular schoolgirl Jenna Rink makes an unusual wish on her birthday. Miraculously, her wish comes true and the 13-year-old Jenna wakes up the next day as a 30-year-old woman.
Director: Gary Winick | Stars: Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis
Votes: 216,981 | Gross: $57.23M
14. Miss Congeniality (2000)
PG-13 | 109 min | Action, Comedy, Crime
An F.B.I. Agent must go undercover in the Miss United States beauty pageant to prevent a group from bombing the event.
Director: Donald Petrie | Stars: Sandra Bullock, Michael Caine, Benjamin Bratt, Candice Bergen
Votes: 230,373 | Gross: $106.81M
15. Serendipity (2001)
PG-13 | 90 min | Comedy, Romance
A couple search for each other years after the night they first met, fell in love, and separated, convinced that one day they'd end up together.
Director: Peter Chelsom | Stars: John Cusack, Kate Beckinsale, Jeremy Piven, Bridget Moynahan
Votes: 121,399 | Gross: $50.29M
16. Something's Gotta Give (2003)
PG-13 | 128 min | Comedy, Drama, Romance
A swinger on the cusp of being a senior citizen with a taste for young women falls in love with an accomplished woman closer to his age.
Director: Nancy Meyers | Stars: Jack Nicholson, Diane Keaton, Keanu Reeves, Amanda Peet
Votes: 129,207 | Gross: $124.73M
17. Maid in Manhattan (2002)
PG-13 | 105 min | Comedy, Drama, Romance
A Senatorial candidate falls for a hotel maid, thinking she is a socialite, when he sees her trying on a wealthy woman's dress.
Director: Wayne Wang | Stars: Jennifer Lopez, Ralph Fiennes, Natasha Richardson, Stanley Tucci
Votes: 96,214 | Gross: $94.01M
18. 50 First Dates (2004)
PG-13 | 99 min | Comedy, Drama, Romance
Henry Roth is a man afraid of commitment until he meets the beautiful Lucy. They hit it off and Henry think he's finally found the girl of his dreams until discovering she has short-term memory loss and forgets him the next day.
Director: Peter Segal | Stars: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin
Votes: 382,296 | Gross: $120.91M
19. Bewitched (2005)
PG-13 | 102 min | Comedy, Fantasy, Romance
Thinking he can overshadow an unknown actress in the part, an egocentric actor unknowingly gets a witch cast in an upcoming television remake of the classic sitcom Bewitched (1964).
Director: Nora Ephron | Stars: Nicole Kidman, Will Ferrell, Shirley MacLaine, Michael Caine
Votes: 75,510 | Gross: $62.25M
20. 27 Dresses (2008)
PG-13 | 111 min | Comedy, Romance
After serving as a bridesmaid 27 times, a young woman wrestles with the idea of standing by her sister's side as her sibling marries the man she's secretly in love with.
Director: Anne Fletcher | Stars: Katherine Heigl, James Marsden, Malin Akerman, Brian Kerwin
Votes: 175,167 | Gross: $76.81M
21. Confessions of a Shopaholic (2009)
PG | 104 min | Comedy, Romance
A college grad lands a job as a financial journalist in New York City to support where she nurtures her shopping addiction and falls for a wealthy entrepreneur.
Director: P.J. Hogan | Stars: Isla Fisher, Hugh Dancy, Krysten Ritter, Joan Cusack
Votes: 83,124 | Gross: $44.28M
22. Coyote Ugly (2000)
PG-13 | 100 min | Comedy, Drama, Music
Aspiring songwriter Violet Sanford, after getting a job at a women-run NYC bar that teases its male patrons, comes out of her shell.
Director: David McNally | Stars: Piper Perabo, Adam Garcia, John Goodman, Maria Bello
Votes: 120,953 | Gross: $60.79M
23. Honey (2003)
PG-13 | 94 min | Drama, Music, Romance
Honey is a sexy, tough music video choreographer who shakes up her life after her mentor gives her an ultimatum: sleep with him or be blacklisted within their industry.
Director: Bille Woodruff | Stars: Jessica Alba, Mekhi Phifer, Romeo Miller, Missy Elliott
Votes: 47,453 | Gross: $30.31M
24. Failure to Launch (2006)
PG-13 | 97 min | Comedy, Romance
A thirty-something is still living with his parents until they hire an interventionist to help him graduate out of the house. That's when the fun begins.
Director: Tom Dey | Stars: Matthew McConaughey, Sarah Jessica Parker, Kathy Bates, Terry Bradshaw
Votes: 85,846 | Gross: $88.72M
25. How to Lose a Guy in 10 Days (2003)
PG-13 | 116 min | Comedy, Romance
Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days.
Director: Donald Petrie | Stars: Kate Hudson, Matthew McConaughey, Adam Goldberg, Kathryn Hahn
Votes: 270,128 | Gross: $105.81M
26. Keeping the Faith (2000)
PG-13 | 128 min | Comedy, Drama, Romance
Two friends, a priest and a rabbi, fall in love with the same woman they knew in their youth, but the religious position of both men denies them romance.
Director: Edward Norton | Stars: Ben Stiller, Edward Norton, Jenna Elfman, Anne Bancroft
Votes: 53,234 | Gross: $37.05M
27. The Devil Wears Prada (2006)
PG-13 | 109 min | Comedy, Drama
A smart but sensible new graduate lands a job as an assistant to Miranda Priestly, the demanding editor-in-chief of a high fashion magazine.
Director: David Frankel | Stars: Anne Hathaway, Meryl Streep, Adrian Grenier, Emily Blunt
Votes: 467,278 | Gross: $124.74M
28. Shaun of the Dead (2004)
R | 99 min | Comedy, Horror
The uneventful, aimless lives of a London electronics salesman and his layabout roommate are disrupted by the zombie apocalypse.
Director: Edgar Wright | Stars: Simon Pegg, Nick Frost, Kate Ashfield, Lucy Davis
Votes: 594,132 | Gross: $13.54M
29. What Women Want (2000)
PG-13 | 127 min | Comedy, Fantasy, Romance
A cocky, chauvinistic advertising executive magically acquires the ability to hear what women are thinking.
Director: Nancy Meyers | Stars: Mel Gibson, Helen Hunt, Marisa Tomei, Alan Alda
Votes: 222,391 | Gross: $182.81M
30. Elizabethtown (2005)
PG-13 | 123 min | Comedy, Drama, Romance
During a hometown memorial for his Kentucky-born father, a young man begins an unexpected romance with a too-good-to-be-true stewardess.
Director: Cameron Crowe | Stars: Orlando Bloom, Kirsten Dunst, Susan Sarandon, Alec Baldwin
Votes: 72,709 | Gross: $26.84M
31. 40 Days and 40 Nights (2002)
R | 96 min | Comedy, Romance
After a brutal break-up, a young man vows to stay celibate during the forty days of Lent, but finds the girl of his dreams and is unable to do anything about it.
Director: Michael Lehmann | Stars: Josh Hartnett, Shannyn Sossamon, Paulo Costanzo, Adam Trese
Votes: 75,824 | Gross: $37.95M
32. If Only (2004)
PG-13 | 92 min | Comedy, Drama, Fantasy
It takes a tragedy to teach the young businessman Ian to put love ahead of work and open up to his musician girlfriend Samantha.
Director: Gil Junger | Stars: Jennifer Love Hewitt, Paul Nicholls, Tom Wilkinson, Diana Hardcastle
Votes: 33,792
33. High Fidelity (2000)
R | 113 min | Comedy, Drama, Music
Rob, a record store owner and compulsive list maker, recounts his top five breakups, including the one in progress.
Director: Stephen Frears | Stars: John Cusack, Iben Hjejle, Todd Louiso, Jack Black
Votes: 189,806 | Gross: $27.29M
34. The Hottie & the Nottie (2008)
PG-13 | 91 min | Comedy, Romance
A woman agrees to go on a date with a man only if he finds a suitor for her unattractive best friend.
Director: Tom Putnam | Stars: Paris Hilton, Joel David Moore, Christine Lakin, Johann Urb
Votes: 39,143 | Gross: $0.03M
35. Last Holiday (2006)
PG-13 | 112 min | Comedy, Drama, Romance
Upon learning of a terminal illness, a shy woman decides to sell all her possessions and live it up at a posh Central European hotel.
Director: Wayne Wang | Stars: Queen Latifah, LL Cool J, Timothy Hutton, Giancarlo Esposito
Votes: 36,274 | Gross: $38.36M
36. He's Just Not That Into You (2009)
PG-13 | 129 min | Comedy, Drama, Romance
This Baltimore-set movie of interconnecting story arcs deals with the challenges of reading or misreading human behavior.
Director: Ken Kwapis | Stars: Ginnifer Goodwin, Jennifer Aniston, Jennifer Connelly, Morgan Lily
Votes: 182,277 | Gross: $93.95M
37. View from the Top (2003)
PG-13 | 87 min | Comedy, Romance
A small-town woman tries to achieve her goal of becoming a flight attendant.
Director: Bruno Barreto | Stars: Gwyneth Paltrow, Christina Applegate, Kelly Preston, Mark Ruffalo
Votes: 28,590 | Gross: $15.59M
38. Bride & Prejudice (2004)
PG-13 | 122 min | Comedy, Drama, Musical
A modern adaptation of Jane Austen's classic novel, Pride and Prejudice, that features the lives of four unmarried daughters in an Indian family.
Director: Gurinder Chadha | Stars: Martin Henderson, Aishwarya Rai Bachchan, Nadira Babbar, Anupam Kher
Votes: 21,670 | Gross: $6.61M
39. Bridget Jones's Diary (2001)
R | 97 min | Comedy, Drama, Romance
Bridget Jones is determined to improve herself while she looks for love in a year in which she keeps a personal diary.
Director: Sharon Maguire | Stars: Renée Zellweger, Colin Firth, Hugh Grant, Gemma Jones
Votes: 263,743 | Gross: $71.54M
40. Just Like Heaven (2005)
PG-13 | 95 min | Comedy, Drama, Fantasy
A lonely landscape architect falls for the spirit of the beautiful woman who used to live in his new apartment.
Director: Mark Waters | Stars: Reese Witherspoon, Mark Ruffalo, Donal Logue, Dina Spybey-Waters
Votes: 117,386 | Gross: $48.32M
41. Just Married (2003)
PG-13 | 95 min | Comedy, Romance
A young newlywed couple honeymoon in Europe, where obstacles challenge their ability to sustain the marriage.
Director: Shawn Levy | Stars: Ashton Kutcher, Brittany Murphy, Christian Kane, David Moscow
Votes: 74,395 | Gross: $56.13M
42. Suburban Girl (2007)
PG-13 | 97 min | Comedy, Drama, Romance
A Manhattanite book editor finds her take on the game of romance changed after she lures the attention of an influential older man.
Director: Marc Klein | Stars: Sarah Michelle Gellar, Alec Baldwin, Maggie Grace, James Naughton
Votes: 7,779
43. Rumor Has It... (2005)
PG-13 | 97 min | Comedy, Drama, Romance
Sarah Huttinger is a woman who learns that her family was the inspiration for the book and film "The Graduate" -- and that she just might be the offspring of the well-documented event.
Director: Rob Reiner | Stars: Jennifer Aniston, Mark Ruffalo, Shirley MacLaine, Kevin Costner
Votes: 61,677 | Gross: $43.00M
44. My Boss's Daughter (2003)
PG-13 | 86 min | Comedy, Romance
After a man is asked to house sit for his boss, he becomes determined to get closer to the boss's daughter, but events keep unfolding that stop him from achieving his goal.
Director: David Zucker | Stars: Ashton Kutcher, Tara Reid, Andy Richter, Molly Shannon
Votes: 30,655 | Gross: $15.55M
45. Sex and the City (2008)
R | 145 min | Comedy, Drama, Romance
A New York City writer on sex and love is finally getting married to her Mr. Big. But her three best girlfriends must console her after one of them inadvertently leads Mr. Big to jilt her.
Director: Michael Patrick King | Stars: Sarah Jessica Parker, Kim Cattrall, Cynthia Nixon, Kristin Davis
Votes: 127,285 | Gross: $152.65M
46. The Notebook (2004)
PG-13 | 123 min | Drama, Romance
An elderly man reads to a woman with dementia the story of two young lovers whose romance is threatened by the difference in their respective social classes.
Director: Nick Cassavetes | Stars: Gena Rowlands, James Garner, Rachel McAdams, Ryan Gosling
Votes: 620,387 | Gross: $81.00M
47. Two Weeks Notice (2002)
PG-13 | 101 min | Comedy, Romance
A lawyer decides that she's used too much like a nanny by her boss, so she walks out on him.
Director: Marc Lawrence | Stars: Sandra Bullock, Hugh Grant, Alicia Witt, Dana Ivey
Votes: 125,949 | Gross: $93.35M
48. Duplex (2003)
PG-13 | 89 min | Comedy
A young couple has a chance to move into a gorgeous duplex in the perfect New York neighborhood. All they have to do is bump off the current tenant, a cute little old lady.
Director: Danny DeVito | Stars: Ben Stiller, Drew Barrymore, Eileen Essell, Harvey Fierstein
Votes: 62,000 | Gross: $9.69M
49. My Fake Fiancé (2009 TV Movie)
Not Rated | 95 min | Comedy, Romance
Cash-strapped virtual strangers Jennifer and Vince decide to stage a fake engagement and wedding just for the presents.
Director: Gil Junger | Stars: Melissa Joan Hart, Joey Lawrence, Jason MacDonald, Njema Williams
Votes: 7,402
50. Pizza My Heart (2005 TV Movie)
85 min | Family, Romance
Another modern spin-off of Romeo & Juliet, this time about two families who each run rivaling pizza restaurants in New Jersey.
Director: Andy Wolk | Stars: Shiri Appleby, Eyal Podell, Dan Hedaya, Michael Badalucco
Votes: 1,340
51. Labor Pains (2009)
PG-13 | 89 min | Comedy, Romance
A young woman pretends to be pregnant in order to avoid being fired from her job. When that gets her special treatment by everyone involved in her life, she tries to keep up the lie for nine months.
Director: Lara Shapiro | Stars: Lindsay Lohan, Luke Kirby, Chris Parnell, Aaron Yoo
Votes: 12,073
52. See Jane Date (2003 TV Movie)
TV-PG | 90 min | Comedy, Romance
A single girl living in New York tries to impress her high school nemesis by inventing the perfect boyfriend as her date to an impending wedding, then embarks on a string of blind dates to fill the bill.
Director: Robert Berlinger | Stars: Charisma Carpenter, Holly Marie Combs, David Lipper, Joshua Malina
Votes: 1,820
53. I Want to Marry Ryan Banks (2004 TV Movie)
PG-13 | 95 min | Comedy, Romance
Ryan Banks' manager and old friend, Todd, comes up with the idea to have Ryan be the bachelor on a reality dating show in order to clean up his image. The only problem is, Todd falls in love with Charlie, the girl to whom Ryan has chosen to propose.
Director: Sheldon Larry | Stars: Jason Priestley, Bradley Cooper, Emma Caulfield Ford, Mark L. Walberg
Votes: 2,067
54. Wedding Crashers (2005)
R | 119 min | Comedy, Romance
John Beckwith and Jeremy Grey, a pair of committed womanizers who sneak into weddings to take advantage of the romantic tinge in the air, find themselves at odds with one another when John meets and falls for Claire Cleary.
Director: David Dobkin | Stars: Owen Wilson, Vince Vaughn, Rachel McAdams, Christopher Walken
Votes: 375,865 | Gross: $209.22M
55. The Sweetest Thing (2002)
R | 84 min | Comedy, Romance
Christina Walters spent years avoiding men, then suddenly met her perfect match while hanging with her best friends, Courtney and Jane. When she finds out that he has left town, she and Courtney set out on a trip.
Director: Roger Kumble | Stars: Cameron Diaz, Thomas Jane, Christina Applegate, Lillian Adams
Votes: 62,472 | Gross: $24.72M
56. A Guy Thing (2003)
PG-13 | 101 min | Comedy, Romance
A soon-to-be husband wakes up on the morning after his bachelor party in bed with another woman.
Director: Chris Koch | Stars: Jason Lee, Julia Stiles, Selma Blair, James Brolin
Votes: 18,367 | Gross: $15.41M
57. My Super Ex-Girlfriend (2006)
PG-13 | 96 min | Comedy, Romance, Sci-Fi
When a regular guy dumps a superhero for her neediness, she uses her powers to make his life a living hell.
Director: Ivan Reitman | Stars: Uma Thurman, Luke Wilson, Anna Faris, Rainn Wilson
Votes: 67,022 | Gross: $22.53M
58. Glitter (2001)
PG-13 | 104 min | Drama, Music, Romance
A young singer dates a disc jockey who helps her get into the music business, but their relationship become complicated as she ascends to super stardom.
Director: Vondie Curtis-Hall | Stars: Mariah Carey, Eric Benét, Max Beesley, Da Brat
Votes: 24,090 | Gross: $4.27M
59. Sweet Home Alabama (2002)
PG-13 | 108 min | Comedy, Romance
A young woman who has reinvented herself as a New York City socialite must return home to Alabama to obtain a divorce from her husband after seven years of separation.
Director: Andy Tennant | Stars: Reese Witherspoon, Patrick Dempsey, Josh Lucas, Candice Bergen
Votes: 123,621 | Gross: $127.22M
60. Penelope (2006)
PG | 104 min | Comedy, Fantasy, Romance
A modern romantic tale about a young aristocratic heiress born under a curse that can only be broken when she finds true love with "one who will accept her as one of their own."
Director: Mark Palansky | Stars: Christina Ricci, James McAvoy, Reese Witherspoon, Richard E. Grant
Votes: 66,230 | Gross: $10.01M
61. Because I Said So (2007)
PG-13 | 102 min | Comedy, Romance
A meddling mother tries to set her daughter up with the right man so her kid won't follow in her footsteps.
Director: Michael Lehmann | Stars: Diane Keaton, Mandy Moore, Gabriel Macht, Tom Everett Scott
Votes: 40,130 | Gross: $42.67M
62. Swept Away (2002)
R | 89 min | Comedy, Romance
A snooty socialite is stranded on a Mediterranean island with a communist sailor.
Director: Guy Ritchie | Stars: Madonna, Adriano Giannini, Bruce Greenwood, Elizabeth Banks
Votes: 17,875 | Gross: $0.01M
63. Win a Date with Tad Hamilton! (2004)
PG-13 | 95 min | Comedy, Romance
A small-town girl wins a date with a male celebrity through a contest. When the date goes better than expected, a love triangle forms between the girl, the male celebrity, and the girl's best friend.
Director: Robert Luketic | Stars: Kate Bosworth, Josh Duhamel, Topher Grace, Nathan Lane
Votes: 29,436 | Gross: $17.07M
64. Meet the Parents (2000)
PG-13 | 108 min | Comedy, Romance
Male nurse Greg Focker meets his girlfriend's parents before proposing, but her suspicious father is every date's worst nightmare.
Director: Jay Roach | Stars: Ben Stiller, Robert De Niro, Teri Polo, Blythe Danner
Votes: 355,230 | Gross: $166.24M
65. Love & Basketball (2000)
PG-13 | 124 min | Drama, Romance, Sport
Monica and Quincy love and play basketball together through many life challenges from childhood to adulthood.
Director: Gina Prince-Bythewood | Stars: Sanaa Lathan, Omar Epps, Glenndon Chatman, Jess Willard
Votes: 24,330 | Gross: $27.44M
66. Blonde Ambition (2007)
PG-13 | 93 min | Comedy, Romance
A young professional woman (Simpson) unwittingly becomes the pawn of two business executives in their bid to oust the head of a mega-conglomerate.
Director: Scott Marshall | Stars: Jessica Simpson, Luke Wilson, Rachael Leigh Cook, Penelope Ann Miller
Votes: 6,185 | Gross: $0.01M
67. Wimbledon (2004)
PG-13 | 98 min | Comedy, Romance, Sport
A pro tennis player has lost his ambition and has fallen in rank to 119. Fortunately for him, he meets a young player on the women's circuit who helps him recapture his focus for Wimbledon.
Director: Richard Loncraine | Stars: Kirsten Dunst, Paul Bettany, Jon Favreau, Sam Neill
Votes: 66,638 | Gross: $17.00M
68. Fever Pitch (2005)
PG-13 | 104 min | Comedy, Drama, Romance
Lindsay is stuck in the middle of her relationship with Ben and his passion for the Boston Red Sox.
Directors: Bobby Farrelly, Peter Farrelly | Stars: Drew Barrymore, Jimmy Fallon, Jason Spevack, Jack Kehler
Votes: 47,775 | Gross: $42.07M
69. Music and Lyrics (2007)
PG-13 | 104 min | Comedy, Music, Romance
A washed up singer is given a couple days to compose a chart-topping hit for an aspiring teen sensation. Though he's never written a decent lyric in his life, he sparks with an offbeat younger woman with a flair for words.
Director: Marc Lawrence | Stars: Hugh Grant, Drew Barrymore, Scott Porter, Nick Bacon
Votes: 107,207 | Gross: $50.57M
70. Charlie's Angels (2000)
PG-13 | 98 min | Action, Adventure, Comedy
Three women, detectives with a mysterious boss, retrieve stolen voice-ID software, using martial arts, tech skills, and sex appeal.
Director: McG | Stars: Cameron Diaz, Drew Barrymore, Lucy Liu, Bill Murray
Votes: 196,342 | Gross: $125.31M
71. Beauty Shop (2005)
PG-13 | 105 min | Comedy
A determined hairstylist (Queen Latifah) competes with her former boss (Kevin Bacon) after opening her own business in Atlanta.
Director: Bille Woodruff | Stars: Queen Latifah, Alicia Silverstone, Djimon Hounsou, Andie MacDowell
Votes: 18,677 | Gross: $36.35M
72. The Jane Austen Book Club (2007)
PG-13 | 106 min | Comedy, Drama, Romance
Six Californians start a club to discuss the works of Jane Austen, only to find their relationships -- both old and new -- begin to resemble 21st century versions of her novels.
Director: Robin Swicord | Stars: Kathy Baker, Hugh Dancy, Amy Brenneman, Maria Bello
Votes: 29,084 | Gross: $3.58M
73. Did You Hear About the Morgans? (2009)
PG-13 | 103 min | Comedy, Drama, Romance
In New York City, an estranged couple who witness a murder are relocated to small town Wyoming as part of the Witness Protection Program.
Director: Marc Lawrence | Stars: Hugh Grant, Sarah Jessica Parker, Sam Elliott, Elisabeth Moss
Votes: 42,795 | Gross: $29.58M
74. Kissing Jessica Stein (2001)
R | 97 min | Comedy, Drama, Romance
A woman searching for the perfect man instead discovers the perfect woman.
Director: Charles Herman-Wurmfeld | Stars: Jennifer Westfeldt, Heather Juergensen, Tovah Feldshuh, Esther Wurmfeld
Votes: 17,440 | Gross: $7.02M
75. Kate & Leopold (2001)
PG-13 | 118 min | Comedy, Fantasy, Romance
An English Duke from 1876 is inadvertently dragged to modern day New York where he falls for a plucky advertising executive.
Director: James Mangold | Stars: Meg Ryan, Hugh Jackman, Liev Schreiber, Breckin Meyer
Votes: 89,089 | Gross: $47.12M
76. Good Luck Chuck (2007)
R | 96 min | Comedy, Romance
In order to keep the woman of his dreams from falling for another guy, Charlie Logan has to break the curse that has made him wildly popular with single women: Sleep with Charlie once, and the next man you meet will be your true love.
Director: Mark Helfrich | Stars: Dane Cook, Jessica Alba, Dan Fogler, Connor Price
Votes: 94,496 | Gross: $35.02M
77. My Sassy Girl (2001)
Not Rated | 137 min | Comedy, Drama, Romance
A young man sees a drunk, cute woman standing too close to the tracks at a metro station in Seoul and pulls her back. She ends up getting him into trouble repeatedly after that, starting on the train.
Director: Jae-young Kwak | Stars: Cha Tae-hyun, Jun Ji-hyun, In-mun Kim, Song Wok-suk
Votes: 50,503
78. My Sassy Girl (2008)
PG-13 | 92 min | Comedy, Drama, Romance
A sweet Midwestern guy with his life planned out for himself is wooed, groomed, and ultimately dumped by a complicated, elusive gal.
Director: Yann Samuell | Stars: Elisha Cuthbert, Jesse Bradford, Austin Basis, Chris Sarandon
Votes: 20,476
79. Gloss (2007)
118 min | Comedy, Drama
A pretty, young girl from a coal-mining town comes to Moscow with dreams of becoming a supermodel in this satirical look at the fashion industry.
Director: Andrey Konchalovskiy | Stars: Yuliya Vysotskaya, Irina Rozanova, Aleksandr Domogarov, Efim Shifrin
Votes: 1,132
80. Toi et Moi (2007 Video)
3 min | Short, Music
Scream Club enters a hot pink fantasy world with dance offs and drag queens featuring some of Portland's hottest queer glitterati.
Director: Ali Cotterill | Stars: Sarah Adorable, Cindy Wonderful
81. Chronic Bachelor (2003)
Not Rated | 154 min | Comedy, Drama
Satyapratapan (Mammootty) and Kuruvila (Innocent) are chronic bachelors. Sp's sister Sandhya lives as a paying guest in their neighbourhood. Problems begin when Mukesh and Harishree Ashokan join Mammootty and Rambha joins Sandhya.
Director: Siddique | Stars: Mammootty, Mukesh, Rambha, Bhavana
Votes: 880
82. Committed (I) (2000)
R | 98 min | Comedy, Drama, Romance
A young woman goes in search of her midlife crisis suffering husband who left her.
Director: Lisa Krueger | Stars: Heather Graham, Casey Affleck, Luke Wilson, Goran Visnjic
Votes: 4,045 | Gross: $0.04M
83. The Guru (2002)
R | 94 min | Comedy, Music, Romance
A young man leaves India to find fame and fortune in America where he unexpectedly becomes a sex guru.
Director: Daisy von Scherler Mayer | Stars: Jimi Mistry, Heather Graham, Marisa Tomei, Michael McKean
Votes: 15,503 | Gross: $3.03M
84. Say It Isn't So (2001)
R | 95 min | Comedy, Romance
Jo and Gilly date. They find out they're brother and sister. Jo moves away. Gilly finds out that he's not Jo's brother and that Jo's getting married. Can he stop the wedding in time?
Director: J.B. Rogers | Stars: Chris Klein, Heather Graham, Orlando Jones, Sally Field
Votes: 13,794 | Gross: $5.52M
85. 500 Days of Summer (2009)
PG-13 | 95 min | Comedy, Drama, Romance
After being dumped by the girl he believes to be his soulmate, hopeless romantic Tom Hansen reflects on their relationship to try and figure out where things went wrong and how he can win her back.
Director: Marc Webb | Stars: Zooey Deschanel, Joseph Gordon-Levitt, Geoffrey Arend, Chloë Grace Moretz
Votes: 558,174 | Gross: $32.39M
86. Christmas in Boston (2005 TV Movie)
G | 90 min | Comedy, Romance
Gina and Seth have been pen pals for 13 years and now will have the chance to meet. Both used their best friends pictures to send to each other and now will let their friends meet.
Director: Neill Fearnley | Stars: Marla Sokoloff, Patrick J. Adams, Lindy Booth, Jonathan Cherry
Votes: 2,403
87. Moulin Rouge! (2001)
PG-13 | 127 min | Drama, Musical, Romance
A poor Bohemian poet in 1890s Paris falls for a beautiful courtesan and nightclub star coveted by a jealous duke.
Director: Baz Luhrmann | Stars: Nicole Kidman, Ewan McGregor, John Leguizamo, Jim Broadbent
Votes: 299,406 | Gross: $57.39M
88. Lars and the Real Girl (2007)
PG-13 | 106 min | Comedy, Drama, Romance
A delusional young man strikes up an unconventional relationship with a doll he finds on the Internet.
Director: Craig Gillespie | Stars: Ryan Gosling, Emily Mortimer, Paul Schneider, R.D. Reid
Votes: 155,438 | Gross: $5.97M
89. Return to Me (2000)
PG | 115 min | Comedy, Drama, Romance
A man who falls in love with the woman who received his wife's heart must decide which woman it is who holds his heart.
Director: Bonnie Hunt | Stars: David Duchovny, Minnie Driver, Carroll O'Connor, Robert Loggia
Votes: 22,795 | Gross: $32.66M
90. Romance & Cigarettes (2005)
R | 105 min | Comedy, Musical, Romance
This down-and-dirty musical set in the world of working-class New York tells the story of a husband's journey into infidelity and redemption when he must choose between his seductive mistress and his beleaguered wife.
Director: John Turturro | Stars: James Gandolfini, Susan Sarandon, Kate Winslet, Steve Buscemi
Votes: 12,838 | Gross: $0.54M
91. The Family Stone (2005)
PG-13 | 103 min | Comedy, Drama, Romance
An uptight, liberal businesswoman accompanies her boyfriend to his eccentric and outgoing family's annual Christmas celebration and finds that she's a fish out of water in their free-spirited way of life.
Director: Thomas Bezucha | Stars: Dermot Mulroney, Sarah Jessica Parker, Claire Danes, Diane Keaton
Votes: 75,234 | Gross: $60.06M
92. Surviving Christmas (2004)
PG-13 | 91 min | Comedy, Romance
A lonely, obnoxious young millionaire pays a family to spend Christmas with him.
Director: Mike Mitchell | Stars: Ben Affleck, Christina Applegate, James Gandolfini, Catherine O'Hara
Votes: 27,750 | Gross: $11.66M
93. Just Friends (I) (2005)
PG-13 | 96 min | Comedy, Romance
While visiting his hometown during Christmas, a man comes face-to-face with his old high-school crush and best friend--a woman whose rejection of him turned him into a ferocious womanizer.
Director: Roger Kumble | Stars: Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein
Votes: 127,308 | Gross: $32.62M
94. The Ugly Truth (2009)
R | 96 min | Comedy, Romance
An uptight television producer takes control of a morning show segment on modern relationships hosted by a misogynistic man.
Director: Robert Luketic | Stars: Katherine Heigl, Gerard Butler, Bree Turner, Eric Winter
Votes: 230,462 | Gross: $88.92M
95. What Happens in Vegas (2008)
PG-13 | 99 min | Comedy, Romance
A man and a woman are compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.
Director: Tom Vaughan | Stars: Cameron Diaz, Ashton Kutcher, Rob Corddry, Lake Bell
Votes: 187,913 | Gross: $80.28M
96. Definitely, Maybe (2008)
PG-13 | 112 min | Comedy, Drama, Romance
A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter.
Director: Adam Brooks | Stars: Ryan Reynolds, Rachel Weisz, Abigail Breslin, An Nguyen
Votes: 173,277 | Gross: $31.97M
97. No Reservations (2007)
PG | 104 min | Comedy, Drama, Romance
The life of a top chef changes when she becomes the guardian of her young niece.
Director: Scott Hicks | Stars: Catherine Zeta-Jones, Aaron Eckhart, Abigail Breslin, Patricia Clarkson
Votes: 78,817 | Gross: $43.11M
98. Made of Honor (2008)
PG-13 | 101 min | Comedy, Romance
Hannah surprises Tom, her best friend who is secretly in love with her, with the news of her engagement to a wealthy man. Things take a complicated turn when she asks Tom to be her maid of honor.
Director: Paul Weiland | Stars: Patrick Dempsey, Michelle Monaghan, Kevin McKidd, Kadeem Hardison
Votes: 76,064 | Gross: $46.01M
99. Monster-in-Law (2005)
PG-13 | 101 min | Comedy, Romance
The love life of Charlotte is reduced to an endless string of disastrous blind dates, until she meets the perfect man, Kevin. Unfortunately, his merciless mother will do anything to destroy their relationship.
Director: Robert Luketic | Stars: Jennifer Lopez, Michael Vartan, Jane Fonda, Wanda Sykes
Votes: 65,566 | Gross: $82.93M
100. The Wedding Date (2005)
PG-13 | 90 min | Comedy, Romance
Single-girl anxiety causes Kat Ellis to hire a male escort to pose as her boyfriend at her sister's wedding. Her plan, an attempt to dupe her ex-fiancé, who dumped her a couple years prior, proves to be her undoing.
Director: Clare Kilner | Stars: Dermot Mulroney, Debra Messing, Jack Davenport, Amy Adams
Votes: 56,308 | Gross: $31.73M
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